2-tert-Butoxycarbonylmethyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl ester → 5-Amino-2-tert-butoxycarbonylmethyl-2H-pyrazole-3-carboxylic acid methyl ester

HRID 31531Notes

Reaction equation

HRID 31531 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[N:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1)=[O:4].[H][H]>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[N:7]=[C:8]([NH2:10])[CH:9]=1)=[O:4]

Participants

6

Reactant 2

HCID 586466732-tert-Butoxycarbonylmethyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 586466915-Amino-2-tert-butoxycarbonylmethyl-2H-pyrazole-3-carboxylic acid methyl esterYield 97.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-tert-Butoxycarbonylmethyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl ester (3 gm) in ethyl acetate (60 ml) and acetic acid (4.5 ml) was hydrogenated at 50 psi hydrogen in the presence of 1.5 gm of 10% palladium/carbon for 3 hours. The mixture was then filtered and evaporated to obtain 2.62 gm of pure title product. ESI M+1=256.

Workup

  1. filtrationThe mixture was then filtered
  2. customevaporated

Sources & evidence

ORD record
ord-1e3b61653ac54a748a523ec6ae0b2891
Source dataset
uspto-grants-2008_09
Patent number
US07425640B2

Reaction notes

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